On a call today, an entrepreneur said something that stuck with me: “I win, learn, but never lose.”

It’s a popular phrase — I’ve heard it before — but this time, it hit differently. Probably because I’ve been thinking a lot about the “learn” part.

Everyone loves to talk about winning. And of course, a win/win scenario is ideal. But when things don’t go your way — when you don’t win — the fallback is: “Well, at least I learned something.”

But here's the problem: that only works if you actually learn.

Years ago, I hired someone who proudly claimed to have “10 years of experience.” On paper, it checked out. In practice? Not so much.

What became clear was that he didn’t have ten years of growth — he had two years of poor experience repeated five times.

The same behaviors, the same blind spots, the same poor judgment that got him let go from his last roles showed up again. He had been in business for a decade, but hadn’t learned much about business at all.

And he’s not alone.

A lot of us confuse time spent with wisdom gained. We assume just because we’ve been through something hard, we’ve grown from it. But unless we pause, reflect, and consciously change behavior — we're just rehearsing failure.

True learning only happens when the pain of a mistake leads to a change in how we think, decide, or act.

So yes — win, learn, never lose is a great mindset. But make sure the “learn” part is real.

Because repeating the same lesson over and over isn’t learning — it’s stagnation.

Leadership Takeaway
Create a culture — personally and within your organization — where reflection is baked into the process. After every project, campaign, or tough decision, ask: What worked? What didn’t? What will we do differently next time?

Growth doesn’t come from experience alone. It comes from evaluated experience.

Let’s Make It Personal
What’s one area where you're at risk of repeating the same mistake?